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Synthesis of the enantiomeric 1,4,5,6-tetra-O-benzyl-myo inositols

✍ Scribed by Karol S. Bruzik; Grzegorz M. Salamończyk

Publisher
Elsevier Science
Year
1989
Tongue
English
Weight
490 KB
Volume
195
Category
Article
ISSN
0008-6215

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✦ Synopsis

The synthesis of the optically pure 1,4,5,6-tetra-O-benzyl-myo-inositols was achieved in four steps via diastereomeric 2,3-spire-acetals of myo-inositol with Land D-camphor as the key intermediates. Camphor dimethyl acetal was used for the acetalation reaction. The diastereomers were benzylated and separated by chromatography, and the structures of the products were determined by 2D-NOESY 'H-n.m.r. spectroscopy. Hydrolysis of the diastereomers then afforded the title products. RESULTS AND DISCUSSION Treatment of myo-inositol (1) with a 2-fold molar excess of D-camphor dimethyl acetal (2) in anhydrous methyl sulfoxide at 6S-70" in the presence of a catalytic amount of sulfuric acid gave a mixture of positional and stereoisomers as *Author for correspondence.

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